While it is “legal” to offer the property for sale in this situation, as long as the option is disclosed, it just makes no sense.....unless there is a big piece of the puzzle missing.

There are pieces to the puzzle missing that are eluding all of us that are on this thread. 

If you can get a good deal on a property in the winter I wouldn't worry about the tenant piece of the puzzle.

So another piece of the puzzle is learning how to talk to people.Good luck. 

I am also uncertain if i should approach homeowners who are already under contract with a real estate agent.As you can see i have lots of questions although im somewhat knowledgable it just feels like a whole bunch of puzzle pieces that needs to be put together.if there’s anyone willing to help out I’m sure this post will not only help myself but other beginners who are too shy to ask for help or where to start.

The fact that you have such high vacancy spread over a few properties in different neighborhoods is puzzling.    

Adding things like Netflix/Hulu, board games and puzzles, and any extra little touches really go a long way. 

This is a tricky puzzle here . . . 

I would echo what @Scott Trench says, take a look at XY Planning Network and do a keyword search for the important pieces of your puzzle.

Somethings been puzzling me lately.